Miami Surprised Me: Dive Bars, Street Art, and a City I Completely Misjudged
After a chaotic Sunday in Mexico, I was already scheduled to fly to Miami to spend a few nights with my friend Kathryn. Getting out of town for a few days while things settled back to normal at home felt like exactly the right call.
A City I Had Wrong
I’ll be honest — Miami had never really called to me. I had it filed away in my mind as a place for the ultra-wealthy, full of people trying to out-luxury each other, all gleaming yachts and bottle service and a general competition to be seen. There’s probably lots of that, sure. But what I actually found was a city with serious soul — great dive bars, a rich and vibrant Latino culture, extraordinary street art, delicious food, and genuinely warm people everywhere we went. Miami, I owe you an apology.
Night One: South Beach Bar Hopping
We started on South Beach, working our way through a few very different spots in one night. First stop was Azteca, a Mexican cocktail bar with delicious mezcal drinks. Then on to an Irish dive bar for a change of pace and some catching up. And finally — the discovery of the trip — Mac’s Club Deuce.
If you don’t know Mac’s, let me paint the picture (because I certainly didn’t take any there!!). Miami’s oldest bar, celebrating 100 years in 2026, Mac’s is the antithesis of everything South Beach is supposed to be — dark, laid-back, unchanged for decades, the kind of place that belongs to everyone from a celebrity to a street hustler equally. Anthony Bourdain loved it, and you can immediately understand why. The layout is one of the best bar configurations I’ve ever seen, with seating arranged so you can see basically everyone else at the bar at once. Premium people watching doesn’t begin to cover it.
We ended up back at Mac’s three out of our four nights. Every time was its own experience. Conveniently close by is La Sandwicherie, which became a perfect late-night stop to soak up the evening before heading to bed. Highly recommend the combination.
Day Two: Beach Time and Little Havana
After the first night we needed a slow morning, and the beach delivered exactly that. Lazy, warm, unhurried — exactly what we needed. Then we made our way over to Little Havana.
Little Havana is a neighborhood that moves to its own rhythm. Music spills out of bars onto the street, murals bring color to every surface, and the energy is festive and community-rooted in a way that feels completely genuine. Our favorite spot was Ball and Chain — a beautiful, storied venue where we settled in for live Latin jazz.
Day Three: Cuban Food, Wynwood Murals, and a Banyan Tree
We started the day with lunch at Las Olas Cafe — a classic Cuban meal that hit exactly right before an afternoon on our feet.
Then came the Wynwood mural tour. I often skip guided tours and wondered if I really needed one for this occasion. However, in Wynwood, it helps. The murals are spread across the whole neighborhood, and without a guide you’d miss a lot of them. Ours happened to be a mural artist himself, which added a layer of insight and passion to everything he showed us.
What we weren’t prepared for was the emotional weight of parts of the tour. He walked us past some of the most extraordinary, beautiful pieces in the neighborhood — and then told us they’ll be torn down. Condos, chain stores, development. The story of Wynwood is, in many ways, the story of gentrification at its most visible — because here, what’s being lost is right there on the walls, in full color, for everyone to see. It was devastating and beautiful in equal measure, and I’m glad we went.
That evening we made our way to ZeyZey, an outdoor venue — open air, gorgeous, anchored by an enormous banyan tree at its center that sets the whole tone. We were there to see ((( O ))), also known as June Marieezy, a Filipino-American singer, songwriter, and experimental R&B artist. She was a beautiful spirit and her voice matched the surroundings perfectly.
We capped the night at Churchills, another great dive bar where we caught a set from the Pentagram String Band out of Kansas City — high energy, completely fun, and exactly the kind of unexpected musical discovery that makes a trip.
Last Day: The South Pier, Art Deco, and Makaya McCraven
We squeezed every bit out of our last day. More beach time first, then a walk down to the South Pier — a beautiful stretch of path where you pass volleyball games, people working out, cyclists, everyone just out enjoying life in the sun. Walking back we took our time along Ocean Drive, taking in the Art Deco buildings that line the street. I was genuinely impressed by how beautifully preserved they are — ornate, pastel, distinctly of another era.
Happy hour at Maxine’s Bistro at the Catalina Hotel was the perfect way to transition into the evening before heading to the Bandshell for Makaya McCraven, playing as part of the Montreux Jazz Festival. A great way to end a great trip — and true to form, we added one more classic dive bar to the list: Lost Weekend, a bar packed with pool tables, skeeball, and games, with one of the friendliest bartenders we encountered all trip.
Miami, We’ll Be Back
Miami genuinely surprised me. It’s a city with real layers — the glitzy surface is there if you want it, but underneath is a place with deep Latino roots, a thriving arts scene, a dive bar culture worth celebrating, and people who made us feel welcome everywhere we went. The fact that it’s only four hours from Guadalajara and two hours from Greenville makes it a natural meeting point that I suspect we’ll keep coming back to.
There’s still plenty we didn’t get to. But that feels like a good problem to have.
